Articles, Festivals & special events, Shopping and fashion
Maxwell Street Market
May 18 – Oct. 5, 2025 Free admission • Maxwell Street between Halsted Street and Union Avenue Maxwell Street Market is Chicago’s oldest market, with…
Kelsey O'Connor
73 posts by Kelsey O'Connor
Arts, culture & entertainment, Special events
Celebrate Haitian American Heritage Month in Chicago
Haitian heritage runs deep in Chicago. The city has a special connection to the Caribbean nation — Jean Baptiste Point du Sable, Chicago’s first permanent…
Arts, culture & entertainment, Blog
Fun classes and workshops in Chicago
Chicago is a city filled with talented locals, honing their craft in everything from the art of stained glass to cake decorating to flying trapeze…
Hotels
Hotels near Grant Park in Chicago
One of Chicago’s largest and oldest green spaces, Grant Park is the crown jewel of the downtown lakefront. The park is home to some of…
Articles, Parks & outdoors
Guide to kayaking in Chicago
Chicago is lucky enough to be home to not one, but two stunning waterfronts — the Chicago River and Lake Michigan. Both of these iconic…
Festivals & special events
Chicago House Music Festival and Conference
Aug. 22 – 23, 2025 Free admission • Millennium Park and beyond The Chicago House Music Festival is an annual celebration of Chicago house music…
Blog, Neighborhoods
Spend a day in Chicago’s Hermosa neighborhood
Hermosa is a small neighborhood on Chicago’s northwest side that’s home to a close-knit Hispanic population, local eateries, vintage warehouses, and lots of hidden gems.…
LGBTQ+
LGBTQ+ nightlife in Chicago: gay and lesbian bars, clubs, and more
Chicago’s nightlife is a lot like the city itself — inclusive, diverse, and welcoming to all. It’s also a whole lot of fun. Our gay…
Articles, Bucket list, Itineraries, Parks & outdoors
Things to do in Chicago in the spring
What’s spring like in Chicago? Tulips bloom along iconic Michigan Avenue, cherry blossoms pop up in Jackson Park, and city parks begin to overflow with…
Articles, Hotels
Chicago hotels with rooftop bars
Chicago is a city known for its stunning skyline, and one of the best ways to enjoy it is from the city’s many rooftop bars.…
Blog, Special events
Your guide to the Chicago Auto Show 2025
For car lovers, winter in Chicago can only mean one thing — the Chicago Auto Show. Whether you’re a first-time or an Auto Show veteran,…
Blog, Special events
30+ things to do in Chicago in 2025: concerts, exhibits, festivals, and more
For Chicago, 2024 was a milestone year — the city hosted major gatherings like the Democratic National Convention, welcomed millions of visitors from around the…
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